(3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone

Base Information

• Chemical Name: (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone
• CAS No.: 195196-15-7
• Molecular Formula: C₁₇H₁₇NO₃
• Molecular Weight: 283.327
• Mol file: 195196-15-7.mol

Synonyms:(3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone

Chemical Property of (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone

There total 5 articles about (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

C41H61NO4Si2 (195196-19-1) → (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone (195196-15-7)

Guidance literature:

With hydrogen fluoride; In acetic acid; at 50 ℃;

DOI:10.1021/jo971009v

Reference yield: 6.0%

C30H49NO4Si2 → (3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-phenyl-2-((R)-1-phenyl-ethyl)-isoxazolidin-5-one + (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone (195196-15-7) + (3R,4R)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone + 4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone

Guidance literature:

With hydrogen fluoride; In acetic acid; at 50 ℃;

DOI:10.1021/jo971009v

Reference yield:

(R)-(+)-α-methylbenzylhydroxylamine oxalate (118743-81-0) → (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone (195196-15-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / NaHCO₃, MgSO₄ / tetrahydrofuran / 20 °C

2: 98 percent / ZnI₂ / acetonitrile; CH₂Cl₂ / 1 h / 20 °C

3: 74 percent / aq. HF / acetic acid / 50 °C

With hydrogen fluoride; sodium hydrogencarbonate; magnesium sulfate; zinc(II) iodide; In tetrahydrofuran; dichloromethane; acetic acid; acetonitrile;

DOI:10.1021/jo971009v

upstream raw materials:

C₄₁H₆₁NO₄Si₂

(R)-(+)-α-methylbenzylhydroxylamine oxalate

N-Benzylidene<(R)-(-)-α-methylbenzyl>amine N-oxide

benzaldehyde

Downstream raw materials:

methyl (2S,3S)-2-hydroxy-3-(N-tert-butoxycarbonylamino)-3-phenylpropanoate

methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

(2S,3S)-N-benzoyl-3-phenylisoserine

threo-3-phenylisoserine

Refernces